Reaction #710539

Reaction equation

N-chlorosuccinimide

thioacetic acid S-(4-bromo-benzyl) ester

HCl

Water

→

(4-bromo-phenyl)-methanesulfonyl chloride

Solvents

acetonitrile

acetonitrile

Conditions

Workup

1. 1
   Otherthe reaction
2. 2
   workup.ADDITIONThe remaining solution was added
3. 3
   Otherreaction
4. 4
   workup.WAITleft
5. 5
   Temperatureto warm to room temperature for 10 minutes
6. 6
   TemperatureThe mixture was cooled to 0° C.
7. 7
   Extractionthe product was extracted with EtOAc
8. 8
   Washwashed with brine
9. 9
   Dryingdried with Na2SO4
10. 10
    Concentrationconcentrated

Procedure

To a solution of N-chlorosuccinimide (3.95 g, 29.6 mmol) in acetonitrile (11.6 mL) and 1 M HCl (2.31 mL) at 0° C. was slowly added a solution of thioacetic acid S-(4-bromo-benzyl) ester (1.81 g, 7.39 mmol) in acetonitrile (6.3 mL) over 60 minutes whilst allowing the reaction to warm to 15° C. The remaining solution was added and reaction left to warm to room temperature for 10 minutes. The mixture was cooled to 0° C. and stirred for 1 hour. Water was added and the product was extracted with EtOAc, washed with brine, dried with Na2SO4, concentrated to give (4-bromo-phenyl)-methanesulfonyl chloride (2.6 g, 9.6 mmol). 1H NMR (300 MHz, CDCl3): δ 7.60 (d, 2 H), 7.36 (d, 2 H), 4.81 (s, 2 H).

Source